CN107737043B - Hyaluronic acid-based tea polyphenol-loaded self-assembled nano-composite, and preparation method and application thereof - Google Patents
Hyaluronic acid-based tea polyphenol-loaded self-assembled nano-composite, and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a hyaluronic acid-based tea polyphenol-loaded self-assembled nano composite, which comprises a PEG hyaluronic acid polymer system carrier and tea polyphenol loaded on the carrier, wherein the encapsulation rate of the tea polyphenol is 30-60%, and the drug-loading rate expressed by mass ratio is 5-10%. The invention also discloses a preparation method of the self-assembly nano composite. Based on the current situation that tea polyphenol is unstable in application of daily chemical products, the invention adopts polymer PEG water-soluble high molecular hyaluronic acid as a carrier, and tea polyphenol is encapsulated by a self-assembled nano structure to form a stable system, so that the tea polyphenol is free from layering and precipitation after being stored for a certain time at room temperature, and the problem of easy oxidation and discoloration of the tea polyphenol in the application of daily chemical products is solved. And the preparation is simple.
Description
Technical Field
The invention relates to a hyaluronic acid loaded self-assembly complex of tea polyphenols, a preparation method thereof and application of the complex.
Background
With the increasing level of substances, the demand for personal skin care products is becoming more and more refined. The traditional method for resisting the attack of wind-cold dryness is changed into the method for meeting the requirements on the effects of whitening, sun protection, aging resistance and the like. With the prevalence of natural skin care and other ideas, plant-derived natural active substances are favored by people as main functional ingredients. Therefore, substances with the effects of resisting oxidation, resisting aging and the like are better applied to personal skin care products, high-end daily chemical products are developed, and the cosmetic has good market value. The demand of consumers on the efficacy of daily chemical products becomes mainstream, and the deep development of the efficacy components is of great significance.
Tea polyphenol is the main active component in tea and has strong biological activity. A large number of research data show that the tea polyphenol has various health care and pharmacological actions of resisting oxidation, eliminating free radicals, resisting cardiovascular diseases, inhibiting bacteria, diminishing inflammation and the like. Has good application value in the aspect of skin care, such as astringency, bacteriostasis, ultraviolet resistance, aging resistance and the like. However, because of poor stability, when added into a cream preparation and the like, oxidation easily occurs to cause color change of a finished product, and the shelf life is influenced, so that the application of the product in daily chemical products is limited.
The nano drug-loading system is a drug delivery system with the particle size of 1-1000 nm formed by drugs and nano carriers. Hyaluronic acid, also known as Hyaluronic Acid (HA), is a mucopolysaccharide widely found in the intercellular spaces of vertebrate tissues, and is a linear macromolecular chain composed of (1 → 4) -O- β -D-glucuronic acid- (1 → 3) -N-acetylglucosaminyl disaccharide units, which is expanded in an aqueous solution into a random coil shape, with a coil diameter of about 500 nm. Hyaluronic acid is a proteoglycan component widely existing in extracellular matrix, has good biocompatibility, and is expected to become an ideal carrier material for sustained-release and controlled-release drugs. However, the physical and biological characteristics of easy water solubility, rapid absorption and short residence time in tissues limit the use of the drug carrier in preparation of drug carriers with certain requirements on stability, and the drug carrier needs to be subjected to chemical crosslinking modification to prolong the degradation time and improve the stability. Researches show that HA molecules can be self-assembled into a nano structure after being modified by polymers, so that more drugs are entrapped and a more stable structure is formed.
The development of multiple disciplines such as chemical engineering, biomedicine, polymer materials science, phytochemistry and the like provides power and a source for the technical innovation of daily chemical products; the fusion of biotechnology, nanotechnology, gene recombination technology, enzyme engineering technology, information technology and other technologies points the way for the technological innovation of daily chemical products. The hyaluronic acid and the tea polyphenol are compounded, so that the hyaluronic acid and the tea polyphenol not only have the properties of component materials, but also can obtain the properties which are not possessed by the component materials, and can be widely applied.
Disclosure of Invention
The invention aims to solve the technical problem of providing a hyaluronic acid loaded tea polyphenol self-assembly nano compound with stable performance, a preparation method of the compound with simple and safe process and short treatment period, and application of the compound.
In order to solve the technical problems, the invention firstly discloses a hyaluronic acid-based tea polyphenol-loaded self-assembled nano composite, which comprises a PEG hyaluronic acid polymer system carrier and tea polyphenol loaded on the carrier, wherein the encapsulation rate of the tea polyphenol is 30-60%, and the drug-loading rate expressed by mass ratio is 5-10%.
Further, the hydrodynamic diameter of the self-assembled nano composite is 100-500 nm.
Furthermore, the weight ratio of the components is 0.5-10: 8-40: 10-30: 0.1-1 of catalyst, hyaluronic acid, PEG, tea polyphenol and a proper amount of distilled water,
the hyaluronic acid and PEG form a PEG HA high molecular system under the action of a catalyst in distilled water, the PEG HA high molecular system and the tea polyphenol are mixed in a vortex manner to form a self-assembled nano compound,
the catalyst is an EDC/NHS catalytic system.
Further, the mass concentration of the catalyst is 0.5-1%.
The invention also discloses a preparation method of the self-assembled nano compound based on the hyaluronic acid loaded tea polyphenol, which comprises the following steps
(1) Dissolving a certain amount of hyaluronic acid to prepare a solution with the mass concentration of 0.1-1%;
(2) stirring, and stirring according to the mass volume ratio g/mL 1 of PEG to hyaluronic acid solution: 100-1: 1000, adding PEG, and fully stirring until the system is transparent and clear;
(3) and under the stirring state, dropwise adding an EDC/NHS catalytic system, and continuously stirring for 24 hours after the dropwise adding is finished for 1 hour;
(4) removing the reaction substrate to obtain a PEG HA high molecular system;
(5) dissolving tea polyphenol with mass concentration of more than or equal to 85% in deionized water to obtain water solution with mass concentration of 0.5-1%;
(6) dropwise adding the tea polyphenol aqueous solution into the PEG HA polymer system in a vortex state according to the volume ratio of the tea polyphenol aqueous solution to the PEG HA polymer system of 1: 20-1: 100, mixing the two, and continuing vortex incubation reaction for 2-5min to obtain a self-assembled nano compound based on hyaluronic acid loaded tea polyphenol preliminarily;
(7) and (3) homogenizing and dispersing the PEGylated HA-TP self-assembly nano-structure system obtained in the step (6) to obtain the uniform and stable hyaluronic acid-loaded tea polyphenol-based self-assembly nano-composite.
Further, the EDC/NHS catalytic system is prepared by fully stirring and dissolving 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS) in deionized water in a mass ratio of 1: 1-1: 5, and continuously stirring to react for 1 h.
Further, the hyaluronic acid in the step (1) is dissolved in distilled water or 0.1-0.4 mol/L sodium acetate buffer solution.
Further, in step (4), the substrate is removed by dialysis, membrane filtration or high-speed centrifugation.
Further, the homogenizing and dispersing treatment method in the step (7) comprises ultrasonic oscillation, shearing or colloid mill treatment
The invention also discloses the self-assembly nano-composite based on the hyaluronic acid loaded tea polyphenol or the self-assembly nano-composite based on the hyaluronic acid loaded tea polyphenol prepared by the method, and the self-assembly nano-composite can be used for daily chemical and pharmaceutical products.
Based on the current situation that tea polyphenol is unstable in application of daily chemical products, the invention adopts polymer PEG water-soluble high molecular hyaluronic acid as a carrier, and tea polyphenol is encapsulated by a self-assembled nano structure to form a stable system, so that the tea polyphenol is free from layering and precipitation after being stored for a certain time at room temperature, and the problem of easy oxidation and discoloration of the tea polyphenol in the application of daily chemical products is solved. The composite not only has the properties of each component material, but also can obtain the properties which are not possessed by each component material, so that the composite can be widely applied. The related polymerized product can be used for daily chemical products, can greatly improve the stability of tea polyphenol products and has the health-care effect of hyaluronic acid, thereby improving the effect of the daily chemical products. The method has the advantages of simple and feasible process and equipment, safe operation, low preparation temperature, short treatment period and the like, and has strong application value in the fields of medicines, daily chemical products and the like.
Drawings
FIG. 1 is a schematic view of the preparation process of the present invention.
Detailed Description
The present invention will be described in further detail with reference to the following detailed description and accompanying drawings.
Example 1:
referring to fig. 1, the preparation of the tea polyphenol self-assembled nanostructure sequentially comprises the following steps:
(1) dissolving 0.5g hyaluronic acid (molecular weight 20 kDa) in 100 ml distilled water in a magnetic stirrer under stirring to obtain 0.5% solution;
(2) keeping the stirring state, adding PEG (molecular weight 2K) according to the mass-volume ratio g/mL of the solution of the PEG and the hyaluronic acid of 1:300, and fully stirring until the system is transparent and clear;
(3) keeping the stirring state, dropwise adding an EDC/NHS catalytic system, and continuously stirring for 24 hours after the dropwise adding is finished for 1 hour;
(4) and separating reaction substrates in the PEG-HA polymer system: placing the reaction mixed system in a dialysis bag (with a molecular weight cut-off of 14 kDa), dialyzing in deionized water/methanol solution for 24h, and then dialyzing in deionized water for 48h to obtain a PEG HA high molecular system;
(5) dissolving 1g of Tea Polyphenol (TP) in 100 ml of deionized water to obtain an aqueous solution with the mass concentration of 1%;
(6) vortex incubation of tea polyphenol self-assembled nanostructures (TP-PEG-HA): taking the tea polyphenol aqueous solution prepared in the step (5) according to the volume ratio of the tea polyphenol aqueous solution to the PEGylated HA polymer system of 1:80, dropwise adding the tea polyphenol aqueous solution to the PEGylated HA polymer system in a vortex state, mixing the tea polyphenol aqueous solution and the PEGylated HA polymer system, and continuing vortex incubation reaction for 2-5min to obtain a preliminary hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite (PEGylated HA-TP self-assembled nano-structure);
(7) and ultrasonic vibration dispersion of the tea polyphenol self-assembly nano structure: and (4) dispersing the PEGylated HA-TP self-assembly nano-structure system obtained in the step (6) in an ultrasonic oscillation environment to obtain a uniform and stable hyaluronic acid-loaded tea polyphenol-based self-assembly nano-composite.
Wherein the EDC/NHS catalytic system is prepared by dissolving 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS) in deionized water in a mass ratio of 1:1.2 through full stirring, and continuously stirring to react for 1 h.
Example 2:
in the embodiment, in the step (1), a certain amount of hyaluronic acid is taken, 0.2mol/L sodium acetate buffer (pH = 4-7) is used as a solvent to prepare an HA solution with a corresponding mass concentration, and a 0.2 μm microporous filter membrane is used for filtering to remove undissolved substances.
In the step (2), a certain amount of polyethylene glycol (PEG) is taken to prepare a PEG solution with the mass concentration of 5% by taking 0.2mol/L sodium acetate buffer solution (pH = 4-7) or deionized water as a solvent, and the PEG solution is filtered by a 0.2 mu m microporous filter membrane to remove undissolved substances. The rest of the preparation method is basically the same as that of the example 1 and is not repeated.
Example 4:
in the method for removing the reaction substrate in step (4) of this example, high-speed centrifugation was performed at a rotation speed of 15000 r/min. The rest steps and methods are the same as those in embodiment 1, and are not described again.
Example 5:
in this example, the homogenized dispersion of step (7) was treated with a colloid mill. The rest steps and methods are the same as those in embodiment 1, and are not described again.
It should be noted that the above mentioned embodiments are only preferred embodiments of the present invention, and that the invention may be modified in a simple manner without departing from the principle of the present invention.
Claims (9)
1. A self-assembled nano-composite based on hyaluronic acid loaded tea polyphenol is characterized in that: the hyaluronic acid microcapsule comprises a PEG hyaluronic acid polymer system carrier and tea polyphenol loaded on the carrier, wherein the encapsulation rate of the tea polyphenol is 30-60%, and the drug loading rate expressed by mass ratio is 5-10%;
the weight ratio of the components is 0.5-10: 8-40: 10-30: 0.1-1 of catalyst, hyaluronic acid, PEG, tea polyphenol and a proper amount of distilled water,
the hyaluronic acid and PEG form a PEG HA high molecular system under the action of a catalyst in distilled water, the PEG HA high molecular system and the tea polyphenol are mixed in a vortex manner to form a self-assembled nano compound,
the catalyst is an EDC/NHS catalytic system.
2. The hyaluronic acid-loaded tea polyphenol-based self-assembled nanocomplex according to claim 1, characterized in that: the hydrodynamic diameter of the self-assembled nano composite is 100-500 nm.
3. The method for preparing the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite according to claim 1, wherein the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite comprises: the mass concentration of the catalyst is 0.5-1%.
4. A method for preparing the hyaluronic acid-loaded tea polyphenol based self-assembled nano-composite according to any one of claims 1 to 3, which is characterized in that: the preparation method comprises
(1) Dissolving a certain amount of hyaluronic acid to prepare a solution with the mass concentration of 0.1-1%;
(2) stirring, wherein the mass volume ratio g/mL of PEG to hyaluronic acid solution is 1: 100-1: 1000, adding PEG, and fully stirring until the system is transparent and clear;
(3) and under the stirring state, dropwise adding an EDC/NHS catalytic system, and continuously stirring for 24 hours after the dropwise adding is finished for 1 hour;
(4) removing the reaction substrate to obtain a PEG HA high molecular system;
(5) dissolving tea polyphenol with mass concentration of more than or equal to 85% in deionized water to obtain water solution with mass concentration of 0.5-1%;
(6) dropwise adding the tea polyphenol aqueous solution into the PEG HA polymer system in a vortex state according to the volume ratio of the tea polyphenol aqueous solution to the PEG HA polymer system of 1: 20-1: 100, mixing the two, and continuing vortex incubation reaction for 2-5min to obtain a self-assembled nano compound based on hyaluronic acid loaded tea polyphenol preliminarily;
(7) and (3) homogenizing and dispersing the PEGylated HA-TP self-assembly nano-structure system obtained in the step (6) to obtain the uniform and stable hyaluronic acid-loaded tea polyphenol-based self-assembly nano-composite.
5. The method for preparing the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite according to claim 4, wherein the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite comprises: the EDC/NHS catalytic system is prepared by fully stirring and dissolving 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and N-hydroxysuccinimide in a mass ratio of 1: 1-1: 5 in deionized water, and continuously stirring to react for 1 h.
6. The method for preparing the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite according to claim 4, wherein the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite comprises: dissolving hyaluronic acid in distilled water or 0.1-0.4 mol/L sodium acetate buffer solution.
7. The method for preparing the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite according to claim 4, wherein the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite comprises: and (4) removing the substrate in the step (4) through dialysis, membrane filtration or high-speed centrifugation.
8. The method for preparing the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite according to claim 4, wherein the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite comprises: the homogenizing and dispersing treatment method in the step (7) comprises ultrasonic oscillation, shearing or colloid mill treatment.
9. The hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite of any one of claims 1 to 3 or the hyaluronic acid-loaded tea polyphenol-based self-assembled nano-composite prepared by the method of any one of claims 4 to 8, which is used for daily chemical and pharmaceutical products.
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| CN109363966A (en) * | 2018-11-02 | 2019-02-22 | 华熙福瑞达生物医药有限公司 | A kind of inclusion compound containing γ-aminobutyric acid, alpha-arbutin and hyaluronic acid |
| CN110393683B (en) * | 2019-07-31 | 2022-07-15 | 中华全国供销合作总社杭州茶叶研究所 | Preparation method and application of tea polyphenol micro-nano complex based on protein carrier |
| CN116251037A (en) * | 2021-12-09 | 2023-06-13 | 华熙生物科技股份有限公司 | Hydrolysis sodium hyaluronate self-assembled structure, and preparation method and application thereof |
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| CN102038652A (en) * | 2011-01-05 | 2011-05-04 | 武汉理工大学 | Melphalan multi-targeted drug carrying system, and preparation method and application thereof |
| CN104338124A (en) * | 2014-09-19 | 2015-02-11 | 重庆医科大学 | Asparaginase-loaded self-assembly polyethylene glycol-hyaluronic acid/cyclodextrin nanoparticles |
| CN107223849A (en) * | 2016-03-23 | 2017-10-03 | 江苏天成生化制品有限公司 | A kind of sorbic acid-Tea Polyphenols composite nanoparticle and its application |
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| CN102038652A (en) * | 2011-01-05 | 2011-05-04 | 武汉理工大学 | Melphalan multi-targeted drug carrying system, and preparation method and application thereof |
| CN104338124A (en) * | 2014-09-19 | 2015-02-11 | 重庆医科大学 | Asparaginase-loaded self-assembly polyethylene glycol-hyaluronic acid/cyclodextrin nanoparticles |
| CN107223849A (en) * | 2016-03-23 | 2017-10-03 | 江苏天成生化制品有限公司 | A kind of sorbic acid-Tea Polyphenols composite nanoparticle and its application |
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